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Find Trails > Wisconsin > Pleasant Prairie > Pleasant Prairie Inline Skating Trails

Pleasant Prairie, WI Inline Skating Trails and Maps

1221 Reviews

Looking for the best Inline Skating trails around Pleasant Prairie?

Find the top rated inline skating trails in Pleasant Prairie, whether you're looking for an easy short inline skating trail or a long inline skating trail, you'll find what you're looking for. Click on a inline skating trail below to find trail descriptions, trail maps, photos, and reviews.

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Activities
Length
Surfaces
Type
61 Results
Activities
Length
Surfaces
Type

Almond Road Bike Path
1.5 mi
State: IL
Asphalt

Bloomingdale Trail (The 606)
2.7 mi
State: IL
Asphalt, Concrete

Busse Woods Trail
11.6 mi
State: IL
Asphalt, Concrete

Chicago Lakefront Trail
19 mi
State: IL
Asphalt, Concrete

Deer Grove Trail
3.9 mi
State: IL
Asphalt

Fox River Trail (IL)
45.7 mi
State: IL
Asphalt, Concrete, Crushed Stone

Glacial Drumlin State Trail (Route of the Badger)
53.2 mi
State: WI
Asphalt, Crushed Stone, Gravel

H.U.M. Trail
3.5 mi
State: IL
Asphalt

Hank Aaron State Trail (Route of the Badger)
15.2 mi
State: WI
Asphalt, Crushed Stone

Illinois Prairie Path
58.52 mi
State: IL
Asphalt, Concrete, Crushed Stone

KR Trail (Route of the Badger)
1.5 mi
State: WI
Asphalt, Boardwalk

Kenosha County Bike Trail (Route of the Badger)
7.9 mi
State: WI
Asphalt

Kenosha Pike Bike Trail (Route of the Badger)
6.95 mi
State: WI
Concrete

Kuhn Road Trail
1.4 mi
State: IL
Asphalt

Lake Andrea Multi-Use Path
2.3 mi
State: WI
Asphalt

Lake Arlington Walking Path
2 mi
State: IL
Asphalt

Meadowbrook Trail (Route of the Badger)
2.4 mi
State: WI
Concrete

Milwaukee RiverWalk
3.1 mi
State: WI
Concrete

New Berlin Recreation Trail
7 mi
State: WI
Asphalt

North Branch Trail
25.5 mi
State: IL
Asphalt
Accordion

North Central DuPage Regional Trail

11.6 mi
State: IL
Asphalt, Crushed Stone

North Shore Channel Trail
8.3 mi
State: IL
Asphalt, Concrete, Dirt

Oak Leaf Trail (Route of the Badger)
123.6 mi
State: WI
Asphalt

Ozaukee Interurban Trail (Route of the Badger)
30.1 mi
State: WI
Asphalt

Palatine Trail
9.6 mi
State: IL
Asphalt, Concrete

Pike River Pathway
6.9 mi
State: WI
Asphalt

Prairie Trail (IL)
26.4 mi
State: IL
Asphalt, Crushed Stone, Dirt, Gravel

Salt Creek Trail (IL)
28.6 mi
State: IL
Asphalt, Cinder, Woodchips

Skokie Valley Trail (Cook County)
2 mi
State: IL
Asphalt

Valley Line Trail
1.1 mi
State: IL
Asphalt

Beerline Trail (Route of the Badger)
3.7 mi
State: WI
Asphalt

Chain O' Lakes Bike Path
3.2 mi
State: IL
Asphalt

Fox River Trail (Route of the Badger)
6 mi
State: WI
Asphalt

Green Bay Trail
6.5 mi
State: IL
Asphalt, Concrete, Crushed Stone

Lake Country Trail
15.2 mi
State: WI
Asphalt

Long Prairie Trail
13.9 mi
State: IL
Asphalt, Crushed Stone

North Shore Bike Path
7.7 mi
State: IL
Asphalt, Crushed Stone

Paul Douglas and Crabtree Preserve Trail System
9.2 mi
State: IL
Asphalt

Poplar Creek Trail
9.5 mi
State: IL
Asphalt

Powerline Trail (WI)
2.8 mi
State: WI
Asphalt

Randall Road Bike Trail
3.9 mi
State: IL
Asphalt

River Bend Trail (Silver Glen Trail)
4.4 mi
State: IL
Asphalt

Robert McClory Bike Path
25.4 mi
State: IL
Asphalt, Concrete, Crushed Stone

Root River Pathway (Route of the Badger)
6.6 mi
State: WI
Asphalt

Seven Waters Bike Trail (Route of the Badger)
18.6 mi
State: WI
Asphalt, Crushed Stone, Gravel

Skokie Valley Trail (Lake County)
9.8 mi
State: IL
Asphalt

Stone Mill Trail
1.5 mi
State: IL
Asphalt

Techny Trail
3 mi
State: IL
Asphalt, Concrete

Union Pacific Recreation Path
1.2 mi
State: IL
Asphalt

West Allis Cross Town Connector (Route of the Badger)
0.9 mi
State: WI
Asphalt

East Northbrook Trail
1.1 mi
State: IL
Asphalt

Kinnickinnic River Trail (Route of the Badger)
2.3 mi
State: WI
Asphalt

Prospect Heights Bike Path
4.2 mi
State: IL
Asphalt

Lake Geneva Bike Path (Route of the Badger)
8.9 mi
State: WI
Asphalt

Ridgefield Trace
8 mi
State: IL
Asphalt

Bull Valley Road Shared-Use Path
1.1 mi
State: IL
Asphalt

Fort Hill Bike Path
2.4 mi
State: IL
Asphalt

Lies Road Trail
2.8 mi
State: IL
Asphalt

North Shore Trail (Route of the Badger)
3 mi
State: WI
Asphalt

Racine County Bike Trail (Route of the Badger)
1.4 mi
State: WI
Asphalt, Concrete

Racine-Sturtevant Trail (Route of the Badger)
3.5 mi
State: WI
Asphalt
Trail Image Trail Name States Length Surface Rating
This bike path sits on the east side of Almond Road between Washington Street and Fairfield Lane in Gurnee. The 8-foot wide asphalt path is used by residents as a spot for exercise and recreation, but...
 IL 1.5 mi Asphalt
Overview The Bloomingdale Trail, part of “The 606” park system, is a 3-mile, elevated rail trail on Chicago’s northwest side. Built on a former rail line, the trail sits 17 feet above four of the...
 IL 2.7 mi Asphalt, Concrete
Overview    The Busse Woods Trail spans the Ned Brown Forest Preserve, a 3,700-acre natural space in the northwestern suburbs of Chicago. The preserve—popularly just called Busse Woods—has a large...
 IL 11.6 mi Asphalt, Concrete
Overview  The Chicago Lakefront Trail is aptly named; it spans 19 miles along the shore of Lake Michigan, going right through downtown Chicago to pass many cultural and tourist attractions...
 IL 19 mi Asphalt, Concrete
The Deer Grove Trail is one of several great Chicagoland trails located in properties of the Forest Preserve of Cook County. Deer Grove is the oldest of all the Cook County preserves. It's comprised...
 IL 3.9 mi Asphalt
Overview The Fox River Trail (FRT) was built on stretches of three former railroads: Chicago, Aurora & Elgin; Aurora, Elgin, & Fox River Electric; and Chicago & North Western. Today, it hosts a...
 IL 45.7 mi Asphalt, Concrete, Crushed Stone
Overview The 53-mile Glacial Drumlin State Trail between Cottage Grove and Waukesha provides a glimpse into the past when glaciers bore down on southeastern Wisconsin in the last Ice Age. Those...
 WI 53.2 mi Asphalt, Crushed Stone, Gravel
The H.U.M. Trail (a.k.a. the Huntley-Union-Marengo Trail) was planned to link all three of its namesake northern Illinois towns, but so far only connects Marengo and Union. Interestingly, the...
 IL 3.5 mi Asphalt
In 1957, baseball legend Hank “The Hammer” Aaron led the Milwaukee Braves to the first of two consecutive World Series appearances and a championship over the usually dominant New York Yankees. In...
 WI 15.2 mi Asphalt, Crushed Stone
Overview The Illinois Prairie Path (IPP) was one of the nation’s first rail-trail conversions. The 58-mile trail consists of five connected trail segments with three main branches that converge...
 IL 58.52 mi Asphalt, Concrete, Crushed Stone
The KR Trail is a new addition to Kenosha County’s growing bike-ped network. The trail picks up where the Kenosha Pike Bike Trail leaves off, in Petrifying Springs Park. From the northwest corner of...
 WI 1.5 mi Asphalt, Boardwalk
Overview The Kenosha County Bike Trail runs for nearly 8 miles in two sections separated by couple miles with the city of Kenosha. About the Route The northern segment runs between 1st St....
 WI 7.9 mi Asphalt
Helping to forge a connection between the northern and southern segments of the Kenosha County Bike Trail, the Kenosha Pike Bike Trail also has plenty to offer in its own right, giving trail users a...
 WI 6.95 mi Concrete
The Kuhn Road Trail starts on Lies Road, at Glenbard North High School and continues south along Kuhn Road, past single-family homes and Friendship Park. The trail officially ends at Barbara O'Rahilly...
 IL 1.4 mi Asphalt
The 2.3-mile multiuse trail wraps around Lake Andrea in Pleasant Springs Park. The trail is an easy walk, run or ride around the lake, and is accessible for a wide range of users. It also helps users...
 WI 2.3 mi Asphalt
Lake Arlington is an artificial lake and popular recreation area in Arlington Heights in Cook County. The park features amenities to interest visitors of all ages and it is a local favorite for family...
 IL 2 mi Asphalt
Meadowbrook Trail parallels Meadowbrook Road offering a useful and convenient off-road route through northwest Waukesha. It begins at a connection to Lake Country Recreation Trail, a 15-mile east-west...
 WI 2.4 mi Concrete
The Milwaukee RiverWalk provides a pleasant way to get around Milwaukee from the Historic Third Ward, through downtown, and north to the Lower East Side. It also has easy connections to three other...
 WI 3.1 mi Concrete
Overview The paved New Berlin Recreation Trail runs straight as an east-west compass bearing for 7 miles through the western Milwaukee suburbs, from New Berlin to Waukesha. While it is void of...
 WI 7 mi Asphalt
Overview The North Branch Trail follows the North Branch of the Chicago River for 25.5 miles through Cook County. The trail was originally a dirt path often used for horseback riding; though it’s...
 IL 25.5 mi Asphalt
Accordion
The North Central DuPage Regional Trail stretches 11.6 miles in four segments between the communities of Wayne in the west and Roselle in the east. This paved, multiuse trail provides residents and...
 IL 11.6 mi Asphalt, Crushed Stone
Overview The North Shore Channel Trail extends 8.3 miles from the junction of Green Bay Road and McCormick Boulevard in northern Evanston to the junction of Lawrence Avenue and Francisco Avenue in...
 IL 8.3 mi Asphalt, Concrete, Dirt
Overview The Oak Leaf Trail is the jewel in the crown of Milwaukee County’s extensive trail system. The trail meanders for 123 miles in and around the city of Milwaukee on a changing terrain of...
 WI 123.6 mi Asphalt
Overview If you’re going to visit the historical communities that lie just west of Lake Michigan, why not use the former route of the venerable interurban railroad? The Ozaukee Interurban Trail...
 WI 30.1 mi Asphalt
The village of Palatine has connected many of its community assets with two long sections of off-road, multi-use trail. The more popular northern section is the one most references call simply and...
 IL 9.6 mi Asphalt, Concrete
The Pike River Pathway is a paved, multiuse trail that parallels the river after which its named through meadows, fields, woods, and residential areas in the Village of Mount Pleasant, WI.  From...
 WI 6.9 mi Asphalt
Overview The Prairie Trail runs the length of McHenry County and is managed by the McHenry County Conservation District. The rail trail spans just over 26 miles from the Wisconsin border and the...
 IL 26.4 mi Asphalt, Crushed Stone, Dirt, Gravel
Closure Notice: Starting 05/01/2023 through 12/31/2026, there will be intermittent trail closures under the Tri-State Tollway (I-294) bridge, spanning from Ogden Ave to 31st St due to ongoing...
 IL 28.6 mi Asphalt, Cinder, Woodchips
The Skokie Valley Trail in Cook County parallels active train tracks in the Village of Skokie, providing easy access to both the Oakton–Skokie and Dempster–Skokie stations on the CTA’s Yellow Line....
 IL 2 mi Asphalt
Just 1 mile long, the Valley Line Trail—also known as the Sauganash Trail—extends between Bryn Mawr Avenue and Devon Avenue in the Chicago neighborhood of Sauganash. Two bridges allow for safe...
 IL 1.1 mi Asphalt
Overview The Beerline Trail, named after the corridor that was once used by freight trains transporting the ingredients for beer to some of Milwaukee’s famous breweries, runs for 3.7 miles through...
 WI 3.7 mi Asphalt
The Chain O' Lakes Bike Path is a paved trail that runs between E. Grand Avenue in Fox Lake and Grant Woods Forest Preserve to the east. The trail parallels the railroad track and Rollins Road/CR 31,...
 IL 3.2 mi Asphalt
The Fox River Trail runs diagonally along its namesake waterway through Waukesha in southeastern Wisconsin (just outside of Milwaukee). A trailhead at the E.B. Shurts Environmental Education Center in...
 WI 6 mi Asphalt
The 6.5-mile Green Bay Trail runs parallel to Chicago's Metra commuter rail line north of the Chicago city limits. Stretching through North Shore towns such as Kenilworth, Winnetka, Highland Park, and...
 IL 6.5 mi Asphalt, Concrete, Crushed Stone
Overview The 15.2-mile Lake Country Trail runs from the western edge of Waukesha to Oconomowoc in Wisconsin’s Lake Country area. Most of the trail was built on a former Milwaukee-Watertown...
 WI 15.2 mi Asphalt
The Long Prairie Trail journeys across the width of agricultural Boone County for nearly 14 miles on the railroad corridor previously used by the Kenosha and Rockford Railroad, later known as the...
 IL 13.9 mi Asphalt, Crushed Stone
The North Shore Bike Path runs for nearly 8 miles between Lake Bluff and Mundelein, paralleling State Route 176 for the path's entire length. The trail is one of dozens in the Chicagoland area, all of...
 IL 7.7 mi Asphalt, Crushed Stone
The Paul Douglas and Crabtree Preserve Trail System connects two large nature preserves in northwestern Cook County. The trail begins at the Old Stover Trailhead in the Crabtree Preserve, near the...
 IL 9.2 mi Asphalt
The Poplar Creek Trail is a 9.5-mile paved loop around Poplar Creek Forest Preserve near Hoffman Estates. The trail has a couple of hills but is otherwise level and makes for a pleasant journey...
 IL 9.5 mi Asphalt
Stretching east-west through the City of Greenfield, the Powerline Trail is a new shared-use path that offers multiple recreation and transportation opportunities for locals and visitors alike. The...
 WI 2.8 mi Asphalt
The Randall Road Bike Trail offers a 4-mile paved north-south route along its namesake roadway in a suburb west of Chicago. A highlight of the journey is the trail's passage through the LeRoy Oakes...
 IL 3.9 mi Asphalt
The 4.4-mile River Bend Trail is so named for the loop of Fox River along which it follows on its eastern end. It's here that you can connect to the scenic Fox River Trail to travel 43 miles along the...
 IL 4.4 mi Asphalt
Overview The Robert McClory Bike Path runs the length of Lake County, knitting together a string of communities on the north shore of Chicago all the way to the Wisconsin border. In 1997, the trail...
 IL 25.4 mi Asphalt, Concrete, Crushed Stone
The Root River Pathway uses a combination of off-road trail and on-road route to form a crescent around the City of Racine. The trail closely follows the bends of the Root River, making it a great...
 WI 6.6 mi Asphalt
Overview The Seven Waters Bike Trail is a scenic corridor stretching more than 18 miles north–south between Burlington and Muskego Lake into Waukesha County. The trail was originally three trails,...
 WI 18.6 mi Asphalt, Crushed Stone, Gravel
Overview The Skokie Valley Trail connects Highland Park in the south to the northern trailhead in Lake Bluff. The entire trail corridor is a rail-with-trail, paralleled by double tracks that sit...
 IL 9.8 mi Asphalt
The Stone Mill Trail runs between Lawrence Road in Harvard and Maxon Road in Chemung. The 1.5-mile, paved trail mostly parallels County Highway 17 (Ramer Road) and active railroad tracks, and will...
 IL 1.5 mi Asphalt
The Techny Trail links downtown Glenview, a charming village northwest of Chicago, with the Techny Basin, a scenic wetlands area adjacent to the West Fork of the Chicago River's North Branch....
 IL 3 mi Asphalt, Concrete
The Union Pacific Recreation Path offers a short route through the Village of Lincolnwood's east side between Devon and Touhy avenues. Following the former Union Pacific Railroad, the rail-trail...
 IL 1.2 mi Asphalt
Although short, the West Allis Cross Town Connector represents an important start to a future link between three trails in Milwaukee County. Currently, the trail begins at a junction with the New...
 WI 0.9 mi Asphalt
The East Northbrook Trail is a 1-mile route through a wooded corridor adjacent to an out-of-service rail corridor in the Village of Northbrook. The trail provides access to residential neighborhoods,...
 IL 1.1 mi Asphalt
Kinnickinnic River Trail (called the KK River Trail by locals) runs just over 2 miles in southern Milwaukee, following the river through a densely populated and industrial corridor. The trail links...
 WI 2.3 mi Asphalt
Prospect Heights has very few sidewalks, so biking, inline skating or walking are moved to the streets or in the parks. Don't underestimate the Prospect Heights Bike Path which is over four miles of...
 IL 4.2 mi Asphalt
Overview The 8.9-mile Lake Geneva Bike Path runs through the scenic resort city, offering connections to many of the community’s amenities. The trail has five unique, color-coded segments. About...
 WI 8.9 mi Asphalt
The Ridgefield Trace is a multi-use pathway that runs through suburban Crystal Lake, Illinois. The trail takes its name from the original Indian trace that once ran along the route of what is now...
 IL 8 mi Asphalt
The Bull Valley Road Shared-Use Path travels along the south side of Bull Valley Road in the city of McHenry, Illinois. The paved path is suitable for non-motorized uses including walking, jogging,...
 IL 1.1 mi Asphalt
The Fort Hill Bike Path trail sits on the north side of Peterson Road/ County Road 20. The trail peels away from the Prairie Crossing Bike Path at Midlothian Road and extends west, passing industries...
 IL 2.4 mi Asphalt
This shared-use path runs east-west through the village of Carol Stream in Du Page county. Sitting on the grassy north side of Lies Road between Fair Oaks Road and Gary Avenue, the path is used as an...
 IL 2.8 mi Asphalt
Racine’s southeastern neighborhoods are home to the North Shore Trail, which extends south to the Racine–Kenosha county line. Because Racine County standardized its signs several years ago, you won't...
 WI 3 mi Asphalt
Helping to extend the excellent network of trails around the city of Racine deeper west into the heart of the county, the Racine County Bike Trail serves as a disconnected addition to the...
 WI 1.4 mi Asphalt, Concrete
The Racine-Sturtevant Trail runs for 3.5 miles from the western side of Racine to near the eastern edge of the Village of Sturtevant. The trail occupies an abandoned rail corridor for most of its...
 WI 3.5 mi Asphalt

Recent Trail Reviews

Great Western Trail (DuPage)

great trail

November, 2024 by jcook1950_tl

trail is in great shape. from villa park westward it goes through residential areas with many road crossings with a bridge over the railroad/highway in lombard. but after that there are few crossings and a natural landscape.
although not shown on the trail map, there is now a trail connection just east of prince crossing road that goes north along the west branch of dupage river and fair oaks road which leads to the north central dupage regional trail at schick road.

read more …

Long Prairie Trail

Disappointed

October, 2024 by deetiffanylb

Like all rails to trails, a good connector for locals but for bike touring, tedious. Boring, straight, only a few peeks of rolling farm land to catch your eye, when it wasn't on the trail - immediately in front of you. Sections of the trail are in jaw-jarring condition. Beware: with leaf litter you can not see the periodic holes, non existent bridge transitions, broken asphalt...you get idea. Sad that some entity can not repair these hazards. We def would not continue west, beyond Poplar Grove. Our bodies can't take it!

read more …

Bloomingdale Trail (The 606)

606

October, 2024 by noxxid

Short trail especially for cyclists, more so a commuter trail. Expect a slow and someone densely populated ride, but excellent views of the neighborhoods.

read more …
Accordion

Glacial Drumlin State Trail (Route of the Badger)

Great trail, but there's a temporary closure

October, 2024 by sarahccaltvedt

We rode about 23 miles round-trip from the Waukesha trailhead on Oct. 12. The asphalt is in pretty good condition, with just a few bumps. However, when we got to the big curve around what used to be a field east of Dousman, we discovered that the field is now a massive construction site, and the trail is closed indefinitely, with no posted detour. We don't take our tandem on roads, so we turned around at that point. I assume that the trail is open west of the construction site, but don't know exactly where.

We didn't ride on the western portion of the trail that day, but it's one of our favorites, especially the part where you bike across the lake.

read more …

North Branch Trail

beautiful trail

October, 2024 by given.sandra

We just completed this paved trail. Absolutely beautiful! It’s whining and bikers, walkers, runners n dog walkers use this trail. We didn’t go fast and loved it.

read more …

Powerline Trail (WI)

New trail, is very smooth. Crossing streets is safe. Slight uphill grade west to east which makes return trip west easy!

October, 2024 by lagerke

New trail, is very smooth. Crossing streets is safe. Slight uphill grade west to east which makes return trip west easy!

read more …

Glacial Drumlin State Trail (Route of the Badger)

There are several areas in which there are tire ruts and the trail is too narrow. Diffently not worth the daily fee of $5.00.

September, 2024 by dq82

There are several areas in which there are tire ruts and the trail is too narrow. Diffently not worth the daily fee of $5.00.

read more …

Robert McClory Bike Path

Thoughts Of This Trail Getting Paved, And The Lack Of People Getting Caught Using Motorized Bikes!

September, 2024 by ij3175974

Good News! This Path Is Finally Going To Get Paved Soon, Between 2025 And 2026. I Can't Wait To See How This Path Turns Out, And I'm Ready For This Trail To Be Like The Kenosha County Bike Trail. I'm Glad They Are Doing This, Because I've Caught Several People Speeding On This Trail With Dirt Bikes, And I Think It's Annoying And Dangerous. The Signs Say No Equestrian, And Motorized Vehicles On The Trail, And People Don't Listen. Till This Day, People Still Ride These Motorized Vehicles On This Trail, Including The Waukegan Savanna Trail, Which Is Connected Right By The Trail Intersection In Beach Park, Right Next To The Lyons Woods Forest Preserve. Today, I Saw This One Person Speeding With A Dirt Bike On The Waukegan Savanna Trail, And I Was About To Film Him And Report Him To The Police. If I Catch More People Doing It, I Will Start Recording, And Reporting It To The Police, Because That Should Be Illegal. Overall, I Ride This Trail Often To Visit The Waukegan Airport, To Do A 10 Mile Round Trip Ride, Just Looking Forward To Seeing This Trail Paved, Hopefully In Spring 2025. Be Safe Guys!

read more …

Hank Aaron State Trail (Route of the Badger)

Nice easy trail

September, 2024 by joenad55

Ran parts of this trail recently. Easy paved trail through wooded area. Some shade in early morning hours.

read more …

Prairie Trail (IL)

Water fountain removed

September, 2024 by elissasteglich

The water fountain noted on the map at Hillside Rd no longer exists. Looks like it was taken out.

read more …

Oak Leaf Trail (Route of the Badger)

Great trail!

September, 2024 by nadia.rasberry01

Well maintained trail, no garbage or anything on the path! Was great for walking with a stroller there was one roughest patch we hit but that was it. Amazing views and a nice breeze from the water. Very active trail, pretty busy area.

read more …

Ozaukee Interurban Trail (Route of the Badger)

This has to be one of the top 2 or 3 bike routes in the greater Milwaukee area.

September, 2024 by zero2epiphany

I have ridden this from Brown Deer to just a bit past Port Washington and still need to do the whole thing. On the Soutern side where it starts its no different than say, Zipline or the Brown Deer connector. But once you start getting close to Cederburg, it starts to shine, with a dip in scenery when you transition through Grafton. Then the trail SHINES BRIGHT right into Port Washington. This and Bugline are probably my favorite rides in the greater Milwaukee area.

read more …
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Explore by Activity

ATV
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